Holiday Midi Skirts

Get ready to sleigh the holiday season with our fabulous collection of holiday midi skirts! Perfect for every festivity under the twinkling lights, these skirts are your go-to for adding that extra dash of glam to your wardrobe. Whether you're sipping cocoa by the fire or tearing up the dance floor at the annual office party, our midi skirts have got you covered. From velvet textures to shimmering sequins, you'll have all eyes on you as you make your grand entrance. So go ahead, strut your stuff and let those holiday vibes shine through with every step!

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Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

A black stretchy knit midi skirt with high-rise fit, ruching, and an asymmetrical high-side slit.

Windsor Low Key Luxe Satin Lace Midi Skirt in Black

$49.90

A black satin midi skirt featuring a high-rise waist and elegant sheer lace panel detailing.

Chic Allure High-Slit Midi Skirt in Burgundy

$29.90

A burgundy knit midi skirt featuring a high-rise waist, front ruching, and an asymmetric high side slit.

Windsor Chic Confidence High Slit Mesh Midi Skirt in Black

$26.90

A black mesh midi skirt featuring a ruched waist, high-rise fit, and dramatic thigh-high front slit.

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Wild At Heart Long Fringe Skirt in Tan

$29.90

(34)

Channel your western side with this trendy-chic skirt that will level up your festival look! It features a high-rise waist, an asymmetric mini-length hem with a form-hugging fit, and long fringe detailing that cascades to your ankles. The stylish fringe design will dance with you to your favorite band! Complete your 'fit with a cropped graphic tee and cowboy boots. Fit & FeaturesHigh-rise waist, Back zipper, hook and eye closure, Asymmetric mini-length hem, Form-hugging fit, Long fringe design, ankle-length hem, Faux suede fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wild At Heart Long Fringe Skirt in Tan | Size: XS | Faux Suede

Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

(14)

Fit & FeaturesStretchy smooth knit-lined fabrication, High-rise fit, Ruching, Asymmetrical high-side slit, Midi length hem, Runs true to size, Shop Matching Crop Top: Bold Staple Long Sleeve Crop Top Free Shipping on All Orders Over $75. | Windsor Bold Staple Ruched Asymmetrical Midi Skirt in Black | Size: S

First Take Micro Slit Mini Skirt in Black

$14.90

(9)

Step out looking like goals in this micro mini skirt with a flirty side slit and bodycon fit that'll get you noticed! Fit & FeaturesStretchy knit fabric, High-rise waist, Side slit, Bodycon silhouette, Micro mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor First Take Micro Slit Mini Skirt in Black | Size: S | Knit Fabric

Sleek Status Faux Leather Mini Skirt in Black

$19.90

(8)

Level up your sleek status with this chic mini skirt made with smooth faux leather fabric to elevate your casual 'fits. It features a high-rise waist, a side slit accent at the hem, and a form-hugging silhouette to highlight your stunning curves. Fit & FeaturesFaux leather fabric, plenty of stretch, High-rise elasticized waist, Side slit, Mini-length hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Status Faux Leather Mini Skirt in Black | Size: XS

Life Of The Party Lace-Up Mini Skirt in Brown

$42.90

(4)

This faux leather skirt gives life to the party vibes! It has lace-up sides that demand attention, a high-rise waist, and a flattering form-hugging fit that shows off your figure. Fit & FeaturesFaux leather fabric, High-rise waist, Back zipper closure, Side lace-ups , Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Life Of The Party Lace-Up Mini Skirt in Brown | Size: M | Leather

Sultry Eye Candy Floral Velvet Mesh Mini Skirt in Black

$29.90

(4)

Be the sultry eye candy in this floral velvet mesh mini skirt! The high-rise waist and bodycon fit add a touch of allure and a flattering fit. Pair with the matching top. Fit & FeaturesFlocked floral velvet pattern, mesh-lined fabric, High-rise waist, Bodycon silhouette, Mini-length hem, Runs true to size, Shop The Matching Top: Sultry Eye Candy Floral Velvet Mesh Bustier Free Shipping on All Orders Over $75. | Windsor Sultry Eye Candy Floral Velvet Mesh Mini Skirt in Black | Size: S | Mesh Fabric

Windsor Chic Confidence High Slit Mesh Midi Skirt in Black

$26.90

(3)

When subtle isn’t the move, this mesh midi skirt delivers. With a thigh-high slit and ruched waist, it’s the kind of style that owns the night and brings the confidence. Fit & FeaturesSheer mesh fabric with knit lining, high stretch, High-rise waist, ruching, Ultra-high front slit, Asymmetric midi-length hem, Flowy fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Confidence High Slit Mesh Midi Skirt in Black | Size: M | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

Windsor After Dark Flutter Mini Skirt in Black

$29.90

(3)

Sleek with a little edge, this mini skirt is made for plans that don’t end early. The smooth knit finish and subtle butterfly detail bring just enough intrigue, while the side slit keeps things flirty without trying too hard. Fit & FeaturesSmooth knit fabric with stretch, Low-rise waist, High front slit with subtle butterfly detailing, Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor After Dark Flutter Mini Skirt in Black | Size: L | Knit Fabric

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Windsor Street Zipper Moment Denim Skirt in Black

$14.97 $39.90
62% off

(3)

This mid-rise denim skirt turns every sidewalk into a runway with bold zipper details that strike the perfect balance between edgy and wearable. Pair it with boots, sneakers, or your boldest top. Fit & FeaturesDenim fabric, Mid-rise waist, Multi-zipper detailing, Structured pleated silhouette, Mini length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Street Zipper Moment Denim Skirt in Black | Size: S

Going Somewhere Wrap Slit Maxi Skirt in Black

$29.90

(3)

Easy confidence, built in. This high-rise skirt hugs smoothly with a slinky double-lined knit and a front wrap slit that brings just enough drama for day or night plans. Fit & FeaturesSlinky double-lined knit fabric with stretch, High-rise waist, Body-skimming silhouette, High front wrap slit for movement, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Going Somewhere Wrap Slit Maxi Skirt in Black | Size: XS | Knit Fabric

Holiday Midi Skirts

Holiday midi skirts are the unsung heroes of winter wardrobes, quietly working overtime to deliver style, comfort, and that little spark of celebration—no matter what your calendar looks like. Think of them as your style safety net for everything from Valentine’s dinner reservations to a last-minute invite for drinks after work. With their just-right length and endless versatility, midi skirts strike the perfect balance between dressed up and effortless, making them a go-to for anyone who wants to look festive without feeling overdone. This season, it’s all about rich textures and eye-catching details: plush velvet that feels like a warm hug, gleaming satin that moves with you, and sequins that catch the light (and compliments) from every angle. Whether you gravitate toward classic pleats, a modern slip silhouette, or something with a little more volume, there’s a holiday midi that fits your vibe. And the best part? These skirts don’t retire when the parties wind down. Pair them with chunky knits and boots for a cozy brunch, or layer with a fitted turtleneck and blazer for those days when you need to look polished but still want to feel like yourself. If you’re shopping for someone else, midi skirts make a thoughtful gift—especially for friends who love to mix things up or are always on the hunt for that one piece that goes with everything. They’re the kind of present that feels personal, but still gives her the freedom to style it her way.

As February settles in and winter lingers, holiday midi skirts offer a playful escape from the cold and gray. There’s something undeniably uplifting about slipping into a skirt windsor style—one that swishes with every step and instantly upgrades even the simplest outfit. This is the season for layering: think a jewel-toned midi paired with a soft cashmere sweater, or a metallic pleated skirt styled with a graphic tee and leather jacket for a little edge. The midi length is a game-changer for transitional weather, giving you coverage and warmth without sacrificing movement or style. And if you’re someone who likes to keep their closet working year-round, holiday skirts are a smart investment. Swap out heels for sneakers, add tights, or throw on a denim jacket when spring rolls around—these pieces are designed to flex with your plans and your mood. For those navigating the “nothing to wear” panic before a big event or searching for a fresh take on winter dressing, a holiday midi skirt is the answer. It’s the kind of piece that feels special but never fussy, ready to go from office parties to cozy nights in without missing a beat. Explore the full range of festive, versatile options on our Holiday Skirts page and discover how easy it is to make every day feel like a celebration—even when it’s just another Tuesday in February.

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